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Startup 2009: Calacanis, Karp on mistakes

Published June 15, 2009 at 10:56 AM

The 10th and final episode of The Deal's Behind the Money online video series on Startup 2009 isn't exactly a "gag reel," but the folks interviewed at the competition do own up to some bloopers when they answer our question, "What's the biggest mistake you ever made as an entrepreneur?"

Jason Calacanis regrets he didn't sell Silicon Alley Reporter at the peak of the dot-com bubble. Daniel Klaus wishes he understood it was OK to make mistakes back when he was 18 and founding his first record label, Passion Music Group, the catalog of which was bought by BMG Music in 1998. David Pakman, now a partner at venerated venture capital firm Venrock, negotiated a deal with AOL when he was co-founder of Myplay that was not only too expensive but also resulted in Yahoo! Inc.'s (NASDAQ:YHOO) rescinding its $200 million offer for the music startup, which was later bought by Bertelsmann AG for only $30 million. David Karp, the 22-year-old founder of multimedia microblogging service Tumblr Inc., got distracted by all the attention focused on the hot startup before he hired a president and other help.

You can watch the video, below, or download it on iTunes. Also below are links to the other nine episodes in The Deal's Behind the Money Startup 2009 series.

The Deal's Behind the Money online video series on Startup 2009 was taped in June on site at the contest during Internet Week New York. The contest was co-sponsored by Silicon Alley Insider and General Catalyst Partners. Technology dealmakers interviewed in the series include:

Jason Calacanis -- the colorful serial entrepreneur who founded Silicon Alley Reporter back in the day, who is now the CEO of Mahalo.com and in between co-founded and sold Weblogs Inc. to AOL for $25 million -- calls Wikipedia founder Jimmy Wales a "poser," not an entrepreneur, for giving up too quickly on a search service Wales touted as a Google killer.

Kevin Ryan -- the former CEO of DoubleClick Inc. and the current co-founder of AlleyCorp -- talks about the New York tech ecosystem that has grown up since the dot-com days.

Dina Kaplan -- Blip.tv co-founder and Founders Club host -- provides a frank analysis of why New York isn't Silicon Valley, pointing to the Big Apple's high real estate prices and lack of an engineering university of Stanford's caliber.

David Karp -- the 22-year-old founder of multimedia microblogging service Tumblr Inc. -- says that adding to the startup's team, including bringing aboard John Maloney as president, has made him happier and the company stronger.

Charlie O'Donnell -- the co-founder of career development site Path101 Inc. and a former analyst at New York venture capital firm Union Square Ventures -- sometimes wishes he never heard of venture capital but, nevertheless, says, "We're always raising money."

David Pakman -- the former CEO of eMusic and the co-founder of Myplay who recently became a partner at venture capital firm Venrock -- says the best entrepreneurs are those who know how to read signals accurately and make changes accordingly.

Daniel Klaus -- the co-founder of Original Signal Recordings/Music Nation Inc. -- describes how the business model for his company evolved from an online music contest to an independent record label, featuring Ingrid Michaelson, The Sounds and others.

George Bell -- managing director of General Catalyst Partners, which ponied up the $25,000 investment for the grand prize and co-sponsored the contest with Silicon Alley Insider -- talks about how he came up with the idea for the competition.

Cheryl Milone -- founder of patent crowd-sourcing pioneer Article One Partners and grand prize winner -- tells us what victory means for her company.

Special thanks to Silicon Alley Insider's Henry Blodget and Julie Hansen for hosting The Deal at Startup 2009 and to my colleagues at The Deal for all their hard work on the series (in alphabetical order): Neil Buchalter (photo editor, video editor), Tom Groppe (executive producer), Chris Kwieraga (photo editor), Vipal Monga (director, video editor), George White (videographer, video editor, producer), Maria Woehr (audio technician, video editor, producer) and Brennen Wysong (copy editor). - Mary Kathleen Flynn

For comments or suggestions about Deal Video please contact mwoehr@thedeal.com.If you would like to embed this video on your website the embed code is:
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